4-DEHYDRO-2-HYDROXY-6-(2-PHENETHYL)TETRAHYDROPYRAN - 1,3-ACYCLIC DIASTEREOSELECTION IN REACTION WITH MEOH AND ITS APPLICATION IN THE SYNTHESIS OF A RACEMIC MEVINOLIN ANALOG

Authors
YADAV VK KAPOOR KK
Citation
Vk. Yadav et Kk. Kapoor, 4-DEHYDRO-2-HYDROXY-6-(2-PHENETHYL)TETRAHYDROPYRAN - 1,3-ACYCLIC DIASTEREOSELECTION IN REACTION WITH MEOH AND ITS APPLICATION IN THE SYNTHESIS OF A RACEMIC MEVINOLIN ANALOG, Indian journal of chemistry. Sect. B: organic chemistry, including medical chemistry, 35(1), 1996, pp. 8-13
Citations number
26
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Indian journal of chemistry. Sect. B: organic chemistry, including medical chemistry → ACNP
ISSN journal
03764699
Volume
35
Issue
1
Year of publication
1996
Pages
8 - 13
Database
ISI
SICI code
0376-4699(1996)35:1<8:4-1D>2.0.ZU;2-6
Abstract
4-Dehydro-2-hydroxy-6-(2-phenethyl)tetrahydropyran (6) and its dimer ( 7) both react with MeOH in the presence of a catalytic amount of cone. HCl to provide 2.4-bismethoxy-6- (2-phenylethyl)tetra-hydropyran with a decent level of 1,3-acyclic diastereoselection in favour of the 4,6 -trans derivative (9a). The ratio of the arabino (9a) and xylo (9b) st ructures was an unprecedent red 4:1. Models to account for the observe d diastereoselectivity are discussed. Further transformation to the 2- oxo derivative and unmasking of the 4-OH function provide a rapid entr y into a racemic mevinolin analog (14).